Halle Berry in Elie Saab, 2002
“Everything about this look is luminous, from Berry’s lit from within glow and glossy pixie cut to her golden lace and mesh gown. It’s glamorous yet there’s a lightness about the look that keeps it from feeling too stuffy or stale. “— Michella Oré, Fashion Commerce Editor
Cher in Bob Mackie, 1986
“Cher’s look by Bob Mackie in 1986 made a splash for so many reasons. She had hoped for a nomination for Mask, but she was snubbed. Instead of staying home, she took the narrative in her own hands and appeared wearing this show-stopping set. I love that she fearlessly owned this unforgettable moment.” — Jaclyn Cohen, Senior Fashion and Accessories Editor
Nicole Kidman in John Galliano for Christian Dior, 1997
“In 1997 it was nearly impossible to upstage Tom Cruise, but Nicole Kidman managed to draw attention away from her wildly famous husband on the Oscars red carpet with this silk dress by John Galliano, who had recently been appointed creative director of Dior. The way she pulls off the color is, of course, what made it so memorable—most people don’t look this smoking hot in chartreuse. Studying it now, though, I’m struck by the fantastical details, like the embroidered flowers and the mink lining. The shape is very ‘90s, but the embellishments feel like they’re from a fairy tale. Kidman was a star before this dress, but it confirmed her role as a major Hollywood player.”—Izzy Grinspan, Deputy Editor
Chloe Zhau in Hermès, 2021
“Chloe Zhao won the Oscar for best director for Nomadland in 2021, making her the first woman of color to take home the award. She accepted the Oscar in a look that I can only inadequately describe as extremely cool: a muted, putty-colored Hermes dress (that was intricately pleated and beaded if you zoomed in) and simple white sneakers. A total subversion of red carpet expectations. Brilliant.”—Leah Chernikoff, Executive Editor
Lauren Hutton in Halston, 1975
“Everything about Lauren Hutton in Halston at the 1975 Oscars is fabulous. I love the sweet, pastel rainbow hues set against the plunging neckline and fluttering skirt of this ’70s silhouette. She knows how to make everything look so cool.” —Camille Freestone, Senior Digital Fashion Writer
Rihanna in Alaïa, 2023
“I really loved Rihanna’s baby bump moment at the 2023 Oscars just after she revealed that she was pregnant at the Super Bowl. Her custom Alaia dress was perfect, especially in the subtle details like the side slits and sheer fabric over her belly.” —Brooke Bobb, Fashion News Director
Claire Danes in Narcisco Rodriguez, 1997
“Claire Danes at the 1997 Oscars is the chicest. This Narcisco Rodriguez look is as cool now as it was then. Love the color, love that it’s a two-piece, love the child-like blue flower reef necklace and earrings with a handkerchief satin bag and thinly strapped crystal sandals.”—Miguel Enamorado, Accessories Director
Diahann Carroll, 1969
“Diahann Carroll could not be more regal and elegant in her blush dress and jewel-adorned cape in 1969. To me, this dress was way ahead of its time and will always be remembered as a classic gown.” —Taylor Anderson, Senior Social Media Manager
Chloë Sevigny in Yves Saint Laurent, 2000
So simple and yet totally cool. Everything else that she wore was perfectly executed—from the retro-ish hair, to the red orange lipstick, to the dramatic diamond necklace. —Laia Garcia-Furtado, Deputy Culture Director
Gwyneth Paltrow in Ralph Lauren, 1999
“Gwyneth Paltrow’s Ralph Lauren gown in 1999 might just be the reason people still say ‘pretty in pink.’ It was understated elegance, yet made an everlasting imprint on pop culture and American fashion. That was also the night she became an Oscar winner, taking home Best Actress for Shakespeare in Love.” —Jaclyn Cohen, Senior Fashion and Accessories Editor
Jennifer Lopez in Valentino, 2003
“The vintage Valentino gown Jennifer Lopez wore to the 2003 Oscars was so old Hollywood with a modern twist. Perfectly — and, for her, minimally — accessorized, the dress made her shine in that beautiful shade of green.”—Miguel Enamorado, Accessories Director
Barbra Streisand in Arnold Scaasi, 1969
“To the first-ever televised Academy Awards in 1969, Barbra Streisand wore this unforgettable sequined pajama pantsuit by Arnold Scaasi. The collar, the bow, the cuffs, the absolute sheerness of it all—it’s still a little shocking and so totally modern. Streisand won that year for Funny Girl, tying with Katherine Hepburn. (That’s the first and only time that’s happened too!)” —Leah Chernikoff, Executive Editor
Michelle Williams in Vera Wang, 2006
“Another great moment for unusual color happened in 2006, when Michelle Williams appeared at the Oscars in a bright yellow dress by Vera Wang. (She was nominated for Best Supporting Actress for Brokeback Mountain.) The color feels botanical—is it saffron? marigold? daffodil?—but unlike many red carpet gowns, this one doesn’t make the wearer look like a walking flower. Instead, the neckline, belt, and fabric at the hips are geometric, maybe even art deco. It’s a thoughtful dress, a smart-girl dress, but one that still telegraphs a ton of joy.”—Izzy Grinspan, Deputy Editor
Faye Dunaway in Theadora Van Runkle, 1968
“Nominated for her role as Bonnie in Bonnie and Clyde in 1968, Faye Dunaway attended the Academy Awards in a black wrap coat with embellished trim by costume designer Theadora Van Runkle. I think the whole thing is so fabulous, down to the slipper shoes. The robe style silhouette, the little evening bag, the sheer black tights—perfection.”—Camille Freestone, Senior Digital Fashion Writer
Fiona Apple in Thierry Mugler, 2000
“The swirly psychedelic prints of the mid to late 90s were important for me personally, but I love this because it’s just so her. I also think that there’s a way to dress when you’re nominated yourself or when you’re supporting someone who is and this is the perfect “supporting a loved one” dress, quietly making a statement in full-on latex. She is perfect to me.”—Laia Garcia-Furtado, Deputy Culture Director
Billie Eilish in Chanel, 2024
“Billie Eilish’s take on a buttoned-up look strikes the right balance between polished and edgy thanks to a crisp white shirt and rumpled knee-high socks. The makeup is sultry, the hair is full of volume, and the aura is slick.”—Michella Oré, Fashion Commerce Editor
Nicole Kidman in Balenciaga, 2007
“Nicole Kidman in Balenciaga from the Nicolas Ghesquière era is one of my all-time favorites. He somehow made a giant bow feel so sleek and cool—perhaps it’s the subtle metallic accents on the edges. And she and her team thought of everything: the hair and makeup are also so strong. I love the idea of matching your lip to your dress.”—Camille Freestone, Senior Digital Fashion Writer
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